Benzyl Bromide → HCID 86663064, compound

HRID 2410853Notes

Reaction equation

HRID 2410853 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([C:19]([O:21][CH3:22])=[O:20])[C:7]2[NH:8][C:9]3[CH:10]=[C:11]([O:17][CH3:18])[CH:12]=[CH:13][C:14]=3[C:15]=2[N:16]=1.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1.CCOC(C)=O>[CH2:23]([N:8]1[C:9]2[CH:10]=[C:11]([O:17][CH3:18])[CH:12]=[CH:13][C:14]=2[C:15]2[N:16]=[C:4]([Br:3])[CH:5]=[C:6]([C:19]([O:21][CH3:22])=[O:20])[C:7]1=2)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 86663065Methyl 2-bromo-7-methoxy-5H-pyrido[3,2-b]indole-4-carboxylate

Product 1

HCID 86663064HCID 86663064, compoundYield 23.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (81 mg, 2 0 mmol) was added to a solution of methyl 2-bromo-7-methoxy-5H-pyrido[3,2-b]indole-4-carboxylate (450 mg, 1.34 mmol) in THF (6 mL) in an ice bath. After 20 min this was removed from the bath and left stirring at RT for 0.5 h. Benzyl bromide (276 mg, 1.61 mmol) was added. After stirring at RT for 3 days, this was diluted with EtOAc, washed with water, brine, and dried over Na2SO4 Removal of the solvent followed by radial chromatography (elution with DCM) afforded methyl 5-benzyl-2-bromo-7-methoxy-5H-pyrido[3,2-b]indole-4-carboxylate (130 mg, 0.31 mmol, 23% yield). MS (ESI) m/z 425.0 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 8.27 (1H, d, J=8.55 Hz), 7.59 (1H, s), 7.17-7.24 (3H, m), 6.97 (1H, dd, J=8.70, 1.98 Hz), 6.88-6.93 (2H, m), 6.84 (1H, d, J=1.83 Hz), 5.67 (2H, s), 3.86 (3H, s), 3.70 (3H, s).

Workup

  1. customAfter 20 min this was removed from the bath
  2. waitleft
  3. stirringAfter stirring at RT for 3 days
  4. washwashed with water, brine
  5. dry with materialdried over Na2SO4 Removal of the solvent
  6. washfollowed by radial chromatography (elution with DCM)

Sources & evidence

ORD record
ord-ab58401c1d6c49e081013ac9bba637fd
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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